4-Anilino-3-nitrobenzoic acid → 3-Amino-4-phenylamino-benzoic acid

HRID 28664

Reaction equation

HRID 28664 reaction equation
[NH:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[N+:17]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Pd]>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 38243664-Anilino-3-nitrobenzoic acid

Product 1

HCID 7738213-Amino-4-phenylamino-benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 4-anilino-3-nitrobenzoic acid (20.1 mmol) in THF (100 mL) was charged with 10% Pd/C (500 mg) and the reaction flask evacuated and subsequently charged with H2 (g) three times. The mixture was stirred vigorously for 12 h after which time it was filtered through diatomaceous earth and the filtrate concentrated in vacuo to give the desired 3-amino-4-anilinobenzoic acid: e.g. 3-amino4-[(3-hydroxyphenyl)amino]benzoic acid.

Workup

  1. customthe reaction flask evacuated
  2. additionsubsequently charged with H2 (g) three times
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-0a653020fe1a4d3f9a6e01a5511e2f2e
Source dataset
uspto-grants-2008_09
Patent number
US07419995B2

Linked notes

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